2-(2,2,3,3,4,4,5,5-Octafluoropenthanoyl)cyclohexanone | 220792-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,2,3,3,4,4,5,5-Octafluoropenthanoyl)cyclohexanone
• 英文别名: 2-(2,2,3,3,4,4,5,5-Octafluoropentanoyl)cyclohexan-1-one
• CAS: 220792-68-7
• 化学式: C₁₁H₁₀F₈O₂
• 分子量: 326.186
• InChiKey: CLQYBRYASHJWHA-UHFFFAOYSA-N

物化性质

• 沸点：
  274.0±40.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2,2,3,3,4,4,5,5-Octafluoropenthanoyl)cyclohexanone 在 硫酸 、 三氟化硼乙醚 、 羟胺 作用下， 以 异丙醇 为溶剂， 反应 15.0h， 生成 4,5,6,7-tetrahydro-3-(1,1,2,2,3,3,4,4-octafluorobutyl)-2,1-benzisoxazole
  参考文献：
  名称：

  2-(多氟酰基)环烷酮与羟胺的反应

  摘要：

  The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group. react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(200207)85:7<1960::aid-hlca1960>3.0.co;2-6
• 作为产物：
  描述：

  环己酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 lithium hydride 作用下， 以 苯 为溶剂， 以51%的产率得到2-(2,2,3,3,4,4,5,5-Octafluoropenthanoyl)cyclohexanone
  参考文献：
  名称：

  Syntheses of Novel 4-Polfluoroalkyl-Substituted 5,6-Oligomethylene Pyrimidines

  摘要：

  含有多氟烷基团的2-酰基环烷酮与胍、尿素、硫脲、甲基异硫脲、苯基胍、氨基硫脲、二氰二胺和三氟乙酰尿素在路易斯酸催化下反应，形成相应的5,6-聚甲烯基嘧啶。观察到随着起始1,3-二酮分子中多氟烷基取代基长度的增加，对于核能性较低的试剂（如尿素、硫脲和二氰二胺），产率下降。由芳香醛获得的嘧啶相较于芳基烯烃双键显示E-构型。通过X射线衍射、红外光谱和核磁共振光谱研究了嘧啶环中2位取代基的变化对其互变异构体结构的影响，涉及液态和固态。

  DOI：

  10.1055/s-2000-8200

文献信息

• Novel polyfluoroalkylated pyrazoles from 2-polyfluoroacylcycloalkanones and hydrazines: syntheses and unequivocal molecular structure assignment
  作者：D V Sevenard、O G Khomutov、M I Kodess、K I Pashkevich、I Loop、E Lork、G -V Röschenthaler

  DOI：10.1139/v01-003

  日期：2001.2.1

  The reaction between 2-trifluoroacetylcycloalkanones and methylhydrazine or phenylhydrazine exclusively yields 3-CF3-pyrazoles. When the chain length of the polyfluorinated substituent in RFC(O) gr...

  2-三氟乙酰环烷酮与甲基肼或苯肼之间的反应仅产生 3-CF3-吡唑。当RFC(O)中多氟取代基的链长...
• ——
  作者：K. I. Pashkevich、D. V. Sevenard、O. G. Khomutov、I. I. Vorontsov

  DOI：10.1023/a:1011317013265

  日期：——

  An efficient procedure for the synthesis of 3-cyano-4-difluoromethyl- and 3-cyano-4-trifluoromethyl-2(1H)-pyridones was developed. The structure of one of the resulting compounds was established by X-ray diffraction analysis.
• Syntheses of Novel 4-Polfluoroalkyl-Substituted 5,6-Oligomethylene Pyrimidines
  作者：Dmitrii V. Sevenard、Oleg G. Khomutov、Olga V. Koryakova、Valeriya V. Sattarova、Mikhail I. Kodess、Johannes Stelten、Ildiko Loop、Enno Lork、Kazimir I. Pashkevich、Gerd-Volker Röschenthaler

  DOI：10.1055/s-2000-8200

  日期：——

  2-Acylcycloalkanones having polyfluoroalkyl groups react with guanidine, urea, thiourea, methylisothiourea, benzamidine, guanylthiourea, dicyanodiamide, and trifluoroacetylurea by Lewis-acid catalysis to form the corresponding 5,6-oligomethylene pyrimidines. A decrease in the yields along with increase of polyfluoroalkyl substituent length in the molecule of the starting 1,3-diketone was observed in the case of reagents with lower nucleophilicity (urea, thiourea, dicyanodiamide). The pyrimidines obtained from aromatic aldehydes showed E-configuration with respect to the arylidene double bond. Tautomeric structures as a function of the substituent in 2 position in the pyrimidine ring both in liquid and solid state were investigated by X-ray diffraction, IR and NMR spectroscopy.

  含有多氟烷基团的2-酰基环烷酮与胍、尿素、硫脲、甲基异硫脲、苯基胍、氨基硫脲、二氰二胺和三氟乙酰尿素在路易斯酸催化下反应，形成相应的5,6-聚甲烯基嘧啶。观察到随着起始1,3-二酮分子中多氟烷基取代基长度的增加，对于核能性较低的试剂（如尿素、硫脲和二氰二胺），产率下降。由芳香醛获得的嘧啶相较于芳基烯烃双键显示E-构型。通过X射线衍射、红外光谱和核磁共振光谱研究了嘧啶环中2位取代基的变化对其互变异构体结构的影响，涉及液态和固态。
• Reaction of 2-(Polyfluoroacyl)cycloalkanones with Hydroxylamine
  作者：Dmitri V. Sevenard、Oleg G. Khomutov、Kazimir I. Pashkevich、Enno Lork、Gerd-Volker Röschenthaler

  DOI：10.1002/1522-2675(200207)85:7<1960::aid-hlca1960>3.0.co;2-6

  日期：2002.7

  The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group. react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis.